Methyl Isocyanate → HCID 44206832, compound

HRID 1029252Notes

Reaction equation

HRID 1029252 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:18]=[CH:17][N:16]=[C:15]3[C:10]=2[C:11]2[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=2[C:13](=[O:19])[NH:14]3)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[N:33]([CH3:36])=[C:34]=[O:35]>CS(C)=O>[CH3:36][NH:33][C:34]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[CH:18]=[CH:17][N:16]=[C:15]3[C:10]=2[C:11]2[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=2[C:13](=[O:19])[NH:14]3)=[CH:6][CH:7]=1)=[O:35]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 81531DiisopropylethylamineHCID 58168047HCID 58168047, compound

Product 1

HCID 44206832HCID 44206832, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

340 (40 mg, 0.13 mmol), DIEA (34 mg, 0.26 mmol), and isocyanatomethane (11 mg, 0.18 mmol) were suspended in DMSO (1 mL), and stirred for 4 h at room temperature. The reaction mixture was quenched with H2O, filtered, washed with H2O and MeOH, and dried under vacuum to provide 342 (23 mg, 46% yield) as a solid. LC-MS (M+H=361, obsd.=361).

Workup

  1. customThe reaction mixture was quenched with H2O
  2. filtrationfiltered
  3. washwashed with H2O and MeOH
  4. customdried under vacuum

Sources & evidence

ORD record
ord-677ed798980447d0adc59657d9d37175
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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